Toluene → 1-[(2,2-Difluorocyclopropyl)methyl]-3-methyl-5-[2-methyl-5-(piperazin-1-yl methyl)phenyl]-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2-dioxide

Participants

Reaction Steps

Tert-butyl 4-(3-{1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridin-5-yl}-4-methylbenzyl)piperazine-1-carboxylate (43-1) (3.3 g, 5.7 mmol, 1.0 eq) was dissolved in DCM (40 mL) and TFA (4.4 mL, 56.7 mmol, 10 eq) was added and the reaction mixture stirred at ambient temperature for 45 minutes. Toluene (10 mL) was added and the reaction mixture was concentrated. The residue was dissolved in EtOAc (100 mL) and then washed with sodium bicarbonate (3×20 mL), water (20 mL) and brine (20 mL), dried over MgSO4, filtered and concentrated to afford 1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-5-[2-methyl-5-(piperazin-1-ylmethyl)phenyl]-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2-dioxide (43-2) as a tan solid. No further purification was necessary. HRMS m/z (M+H) 463.1925 found, 463.1926 required.

Provenance & Evidence